Don’t Use Hope as a Strategy with Sean O'Toole, 1776ing
Summary:
On this episode of Don’t Do That, Kelly Waltrich sits down with Sean O’Toole, founder of 1776ing and CEO of 1776 Wealth, for a conversation about private markets, AI, and why action beats wishful thinking.
Sean went to college on an ROTC scholarship and earned a degree in civil engineering. Four years with the 82nd Airborne at Fort Bragg changed his path. He wanted freedom to build his own way, so he turned down engineering offers and started as a rookie broker at Merrill Lynch. His first years in the business included the Long-Term Capital Management collapse, Y2K panic, and the dot-com crash. He later moved to UBS just ahead of the financial crisis, eventually started his own RIA, 1776 Wealth, and ran a private equity business that grew into 1776ing, an infrastructure platform that helps RIAs access private markets for their clients and helps sponsors find capital.
During the episode, Kelly and Sean dig into the alternatives landscape. Sean explains why he believes wealth is made in private markets and preserved in public ones, shares his concern that the industry is crushing the J curve by selling easy liquidity, and breaks down how fee layers in funds of funds and continuation vehicles eat into returns. He walks through 1776ing’s white-label model, which keeps each sponsor’s brand front and center, and explains why 80-page decks and crowded data rooms don’t work for advisors and their clients. The two also talk AI, including Sean’s view that AI makes the wisdom of experienced professionals more valuable than ever.
Sean’s “don’t do that”: don’t use hope as a strategy. He learned the lesson in the military and says hoping led to nearly all of his failures. He shares how he pictures himself weeks or months in the future, looks back with hindsight, and asks what he can do today instead of waiting for a deal, a market, or a phone call to pave the way.
00:19 – Meet Sean O’Toole
01:29 – From civil engineering and ROTC to the 82nd Airborne
02:48 – Trading engineering offers for a rookie broker seat at Merrill Lynch
04:02 – A volatile start: Long-Term Capital, Y2K, and the dot-com crash
06:56 – Launching an RIA and the private equity business behind 1776ing
08:17 – Adam Smith, The Wealth of Nations, and the story behind the name
11:59 – How Sean sees the alts landscape and where 1776ing fits
17:01 – Why 1776ing runs behind its clients’ brands
19:15 – The J curve and the push for daily and quarterly liquidity
29:11 – How AI makes experienced professionals more valuable
33:17 – Why the “supermarkets of alts” strip away a sponsor’s brand
38:09 – Money-raising businesses versus money-making businesses
41:28 – Sean’s don’t do that: don’t use hope as a strategy
45:27 – Using future hindsight to take action today
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About Our Guest:
Sean O’Toole
Founder and CEO, 1776ing and 1776 Wealth
Sean O’Toole is the founder of 1776ing and CEO of 1776 Wealth. He studied engineering at Worcester Polytechnic Institute and served as an officer in the US Army before spending 20 years in investment banking and financial services with Merrill Lynch and UBS. In 2017, he co-founded 1776 Wealth, an SEC-registered RIA that serves a limited number of families through a deeply integrated advisory team. The rise of crowdfunding sparked his interest in using technology to find better investment opportunities and open them to more people, which led to 1776ing, a SaaS platform built to enable better capitalism for more people. Both companies take their name from 1776, the year Adam Smith published The Wealth of Nations.